Dear Dana: The Guy I Like Isn’t Into Me

Dear Dana is a bi-weekly advice column for humans who engage in romantic relationships. Please send your dilemmas, issues, conundrums, assumptions, conflicts, anxieties, worriments, obstacles, complications, predicaments, queries, questions, and any other synonyms for “problems” to

Dear Dana,

I have had a crush on this boy for a while now and I don’t even think he knows who I am. He’s super popular and a total jock. Me, on the other hand…I do sports, I’m smart, and funny (I think), but I’m not part of the “in” crowd. I’m shy and I’m kind of new at this whole “crushing” thing (I haven’t even been kissed yet).

The boy I like, code name Chimichanga, sits across from me in math and has left some hints that he might possibly like me. The only problem is any attempt of speech with him is flustered and comes out sounding annoyed. Any time he so much as passes me in the hallway, I can feel myself blushing. Like an intense you-need-to-see-a-doctor red.

My best friend knows I like him, so I asked her for advice. I could tell that she didn’t want to hurt my feelings by the look on her face. She said, “You two would be really cute together…tall guys dig shorter girls.” Now I know that just seems like a genuine comment, but the way she said it, I could just tell she doesn’t think I can be with him. I would like the complete and honest truth because that would be very refreshing.

My bestie also said he was once totally checking out my butt. Of course I don’t believe her because there’s no way that a guy who’s super popular like him could ever go out with a small-breasted, shy girl like me. But could he? I want your complete and honest opinion and don’t be afraid to tell me the truth even if it might sting.




Dear Realistic,

There was this guy I liked in high school. He was tall, gorgeous, hilarious, a swimmer, smart, popular, and one day he asked me to skip class with him to go get some Chinese food. He came up to me in the hallway and said, “Skip your next class and let’s go get some Chinese food.” His proximity to me turned my stomach to mush. He only knew me because we were both on the staff of the high school literary magazine and, because I had spent dozens of hours with him, I had forgotten to not speak ever and we had actually had some nice conversations. It was wholly out of character for me to do this, I had never skipped class before. But I forced myself to say, “OK.” And I ran with him, laughing, down the hall, and out into the parking lot.

Twenty minutes later we’re eating pork fried rice in a wooden booth. He starts talking about prom. Like, he’s talking about prom a lot. How he was thinking about going with this one girl but he decided not to anymore because she’s kind of mean and he hates mean people. I agree. He picks at his fried rice and asks me, “Um…are you going to prom?” I say, “Oh, no. No. Prom is stupid. I’m just going to hang out with my other loser friends that night—drive around, get pizza, be lame. You know. Besides, prom is basically a huge waste of money. I went last year and it was boring.” He says, “Oh. OK.” And we start talking about other things as I nervously shove pork friend rice into my mouth because this is the best thing that ever happened to me and I’m desperate for it to be over so I can breathe normally again.

It wasn’t until I was in my car, driving home, that I realized something simultaneously amazing and awful: That boy, the boy who I liked the most, had been about to ask me to prom. He was going to ask me, an unpopular nobody, to prom with him. Until I told him not to.

You are expecting me to tell you that, no, he doesn’t like you, couldn’t ever like you. That is what you are expecting to hear because that is what you’re telling yourself over and over again. It’s what you want me to say because it’s the only answer that you will believe.

You are funny and you are smart. You code named your crush Chimichanga—that shit is great. You are great. Your inner monologue, however—that small stream of words that you say to yourself, quietly, inside of your own head all day—sucks. Your inner monologue is petty and rude and mean and in desperate need of a reality check. Because she is lying to you.

Your inner monologue is not the truth.

I’m going to do what you asked and be very honest with you and tell you a very real truth that most young women aren’t ready to hear at your age: This boy’s opinion of you does not matter. Do not read that last statement as a, “Oh, because he couldn’t ever like me so I should be sad and accept it that I’m not good enough for him.” I AM NOT SAYING THAT. I am saying that if he was looking at your butt, if he hates your pants, if he dreams of you at night, if he doesn’t like the way your hair smells, if he lives for your smiles, if he thinks he heard you fart once, if he loves you for all time: It truly does not matter. Because—and here is a deep, secret truth that most adults do not want to believe because doing so will make the thousands of hours we’ve spent worrying about our own love lives even more pointless than they already are—it only matters whether or not you like him.

The act of liking someone—lighting up when they enter the room, smiling warmly at them, asking them questions and really caring about the answers, enjoying their company, wanting to know more and more about them—is the most seductive power in the world. You clearly and unashamedly liking him will make him like you. I’m not promising you that if you tell him you like him you two will be married. I am saying that everyone thinks that they suck. Even tall, athletic, popular guys think that they suck. And having a funny, smart person lean over and say, “I like you,” is so gorgeous and revelatory that it will shock his shitty inner monologue into complete silence.

Realistic, I want you to allow yourself the gift of liking this guy. Not secretly liking him. Allow yourself to smile at him. Allow yourself to flirt with him. Allow yourself the gift of realizing that he would be lucky to date you. Allow yourself the gift of realizing that he’s probably never seen real live breasts in his life and his primary reaction to your breasts will be eternal gratitude. Allow yourself to know that he doesn’t control when or how this relationship begins. Allow yourself, all of yourself, to know that you are smart and funny, and he is coming to class tomorrow hoping against hope that maybe you’ll smile at him.

Dana Norris once went on 71 internet dates, many of which you may read about here. She is the founder of Story Club and editor-in-chief of Story Club Magazine. She has been featured in McSweeney’s, Role Reboot, The Rumpus, and Tampa Review and she teaches at StoryStudio Chicago. You may find her on Twitter at @dananorris.

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